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Process for producing alpha, beta-unsaturated aldehyde compounds

a technology of aldehyde and unsaturated alcohol, which is applied in the preparation of carbonyl compounds, oxygen-containing compounds, organic chemistry, etc., can solve the problem of unsatisfactory yield of the aimed produ

Inactive Publication Date: 2009-07-02
KAO CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention is about two processes for making certain compounds. The first process involves combining an aldehyde compound with an amine and a protonic acid or salt to create an α,β-unsaturated aldehyde compound. The second process involves reducing the α,β-unsaturated aldehyde compound to create an unsaturated alcohol. These processes can be useful for creating certain compounds that are useful in various applications.

Problems solved by technology

However, the above conventional method has problems such as a relatively large molar ratio of the aldehyde compound (B) to the aldehyde compound (A) (aldehyde compound (B) / aldehyde compound (A)) ranging from 2.5 to 10, necessity of conducting the condensation reaction in a non-polar solvent capable of forming an azeotropic mixture with water, and unsatisfactory yield of the aimed product.

Method used

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  • Process for producing alpha, beta-unsaturated aldehyde compounds
  • Process for producing alpha, beta-unsaturated aldehyde compounds
  • Process for producing alpha, beta-unsaturated aldehyde compounds

Examples

Experimental program
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formulation example

Perfume Composition for Shampoo

[0061]5 parts by mass of sandal mysole core was added to 95 parts by mass of a perfume composition containing respective components shown below, thereby obtaining a perfume composition for shampoo having a sandalwood-like soft scent.

Blending Componentspart by massLinalool15Cyclopentadecanolide12Methyldihydrojasmonate12p-t-Butyl-α-methylhydrocinnamic aldehyde10Cis-3-hexenyl salicylate10Dimethylbenzylcarbinyl acetate5Citronellol5Phenylethyl alcohol5AMBER CORE*5α-n-hexyl cinnamic aldehyde4Benzyl acetate4Orange oil3Linalyl acetate3γ-Methyl ionone2Total95Note:*Tradename of product available from Kao Corporation; compound name: 1-(2-t-butylcyclohexyloxy)-2-butanol

[0062]According to the present invention, α,β-unsaturated aldehyde compounds useful as perfumes or intermediates for perfumes can be produced with high yield and productivity. Further, unsaturated alcohols useful as perfumes, etc., can be produced from the unsaturated aldehyde compounds.

example 1

[0063]A 500 mL four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 171 g (0.98 mol) of campholenic aldehyde (purity: 88%), 3.8 g (0.045 mol) of piperidine and 13.1 g (0.046 mol) of stearic acid, and the contents in the flask were stirred while heating at 100° C. Then, 91 g (1.6 mol) of propionaldehyde was gradually dropped into the flask for 6 h, and the resultant mixture was aged for 1 h and then cooled. Thereafter, 3.2 g (0.053 mol) of acetic acid was added to the mixture to remove amines therefrom, thereby separating the mixture into two layers. The thus separated organic layer was washed with water and separated into two layers, thereby obtaining 295 g (0.93 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 60.6%) (yield based on theoretical amount: 95%).

example 2

[0064]A 500 mL four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 171 g (0.98 mol) of campholenic aldehyde (purity: 88%), 5.8 g (0.045 mol) of dibutyl amine and 5.3 g (0.046 mol) of hexanoic acid, and the contents in the flask were stirred while heating at 100° C. Then, 91 g (1.6 mol) of propionaldehyde was gradually dropped into the flask for 6 h, and the resultant mixture was aged for 1 h and then cooled. Thereafter, 3.2 g (0.053 mol) of acetic acid was added to the mixture to remove amines therefrom, thereby separating the mixture into two layers. The thus separated organic layer was washed with water and further separated into two layers, thereby obtaining 280 g (0.92 mol) of 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-2-en-1-al (purity as measured by gas chromatography: 63.4%) (yield based on theoretical amount: 94%).

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Abstract

The present invention relates to processes for producing α,β-unsaturated aldehyde compounds and unsaturated alcohols with a good yield. There is provided a process for producing and α,β-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the α,β-unsaturated aldehyde compound to a reduction reaction.

Description

FIELD OF THE INVENTION[0001]The present invention relates to processes for producing α,β-unsaturated aldehyde compounds and unsaturated alcohols.BACKGROUND OF THE INVENTION[0002]The α,β-unsaturated aldehyde compounds are useful compounds as perfumes, intermediates for perfumes, or raw materials for medicines or agricultural chemicals.[0003]Examples of the α,β-unsaturated aldehyde compounds usable as perfumes include trans-2-hexenal, trans-2-heptenal, trans-2-octenal, trans-2-nonenal, trans-2-decenal, trans-2-undecenal, trans-2-dodecenal, trans-2-tridecenal, 2,4-octadienal, 2,4-nonadienal, 2,6-nonadienal, 2,4-decadienal, 2,4-undecadienal, 2,4-dodecadienal, citral, α-methylenecitronellal (“Bergamal”), cinnamaldehyde (cinnamic aldehyde), α-methyl cinnamaldehyde and α-hexyl cinnamaldehyde.[0004]Also, examples of the α,β-unsaturated aldehyde compounds usable as the intermediates for perfumes include derivatives of campholenic aldehyde which are usable as a raw material for perfumes such ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C45/45C07C37/20
CPCC07C29/14C07C45/74C07C45/75C07C45/82C07C47/225C07C2101/10C07C33/12C07C47/21C07C47/232C07C49/203C07C47/263C07C2601/10
Inventor ISHIDA, KOSAKUTANAKA, SHIGEYOSHIASADA, TAKAHIRO
Owner KAO CORP